The 5 Wackest Rap Cameos Of All Time

I was wasting my life away on YouTube at 2:00 AM last night, and I discovered that there are some really wack rap cameos out there. One thing lead to another, and so here we find ourselves once again ready to embark on an exciting new journey.

The following is one man’s humble attempt to scientifically quantify these levels of wackness, and to identify the five most offensively wack songs that feature a rap cameo.

Let’s start by outlining some simple criteria, to define the scope of our investigation.

Anything featuring Timbaland, Nelly, Pharrell, and similar artists is exempt from this list. Since these are really more pop artists than actual rappers, and there’s nothing very wack about pop artists having cameo appearances in pop songs by other pop artists, for example Girlfriend by ‘N Sync featuring Nelly or Boys by Britney Spears featuring Pharrell.

Similarly, notoriously promiscuous rap cameo whores like Ja Rule, Fabolous, Jadakiss, and Snoop Dogg are also exempt…because the more you do it, the lower standards are for wackness. It’s hard to be wack when there are no standards for you already.

Also, a full rap cameo is defined as something more substantial than one or two lines in a looping voiceover, for example Timbaland’s chanting in New Republic’s Apologize remix or even his bit in Justin Timberlake’s Cry Me A River.

Remixes – fan made or not – are all inherently wack, and thus disregarded here…but noted as a potential for future study.

Finally, it should be noted here that wackness does not necessarily imply that the quality of the song is detracted from in any way – some of the wackest songs of all time have brought me endless listening pleasure. I happen to love most of the songs on this list, in fact. Regardless, in the end, it still must be noted that they are extremely wack, and concern needs to be paid to the fact that if you do enjoy them…then you are enjoying some wackass songs.

With that in mind, here are the five wackest rap cameos of all time, ordered by degree of wackness. Or basically how shitty the cameo is (or the song overall). A good rule of thumb is to imagine approximately how much money the original artists had to pay or how many favours they had to call in to make it happen. The bigger the sellout, the wacker the cameo.

5) Hey by 3OH!3 featuring Lil’ Jon (2009)
Just barely qualifies as per our above stated criteria. Lil’ Jon collaborating with a super popular, soulless, teen “hip-pop” band with an exclamation mark in their name? This is like saying Madonna and Magic Johnson hooked up in the late 80’s and expecting me to be surprised. I’m still trying to figure out who paid whom in this team-up. Rates extremely low in wackness – I don’t even think he drops a real verse – but there is just something timelessly entertaining about Lil’ Jon in a song called “Hey” doing nothing but screaming stuff “YEAH” and “HEYEAH” with the odd “I DON’T CAREAH” here and there constantly throughout. Honestly, I just wanted to post this one up so that I would have easy access to it in the future. Afford me this indulgence, and let us move on to #4.

4) Numb/Encore by Linkin Park featuring Jay-Z (2004)
How can you say you put 8-balls in corners without using pool sticks and then turn around and party hearty with honksters who have championed the anthem of “Crawling in my skin / These wounds, they will not heal” into the hearts and minds of white, suburban, parent hating, middle class America? Do you really still have any gangster cred left when you decided to make an entire “mashup album” with the guys eventually responsible for the main theme of Transformers 2? On the other hand, both parties are all about making that scratch, and no real strangers to the commercial art of selling out. And this probably made them both truckloads of cash. Jay-Z’s not a businessman, he’s a business, man. I mean in the end…it’s just pop music baby, who cares how wack it is, just get that money and run.

3) Can’t Stop Partying by Weezer featuring Lil’ Wayne (2009)
Pretty much everything Weezer’s done in the last couple of years has been superwack anyway, so it shouldn’t be surprising that they would mess around like this with their “experimental” album. (Didn’t they already do their experimenting with the Red album?) Still, for one of the greatest rock bands of my lifetime, working with a guy like Lil’ Wayne who has made a living off super slick, razor sharp production…on such an underproduced, meh-level song…that is wack as hell. This song also makes my head hurt when I try to imagine a singular party that would feasibly include both Weezer and Lil’ Wayne…I just imagine that club that Forest Whitaker, Jake Gyllenhaal, and Ron Howard are rolling up to at the beginning of Jamie Foxx’s Blame It video.

2) Baby by Justin Bieber featuring Ludacris (2010)
You are shitting me! Really? Is it true Usher and Justin Timberlake were really fighting over the rights to harness the power of the BieberZone? Does that make it okay that Ludacris dropped a verse about how “when he was 13” in this song? I know the man already did a song for Rush Hour 2, but even this is a new ridiculous level of selling out. I mean…

She had me going crazy, oh I was star struck
She woke me up daily, don’t need no Starbucks

…seriously?

1) Radio Song by REM featuring KRS-One (1991)
And the wackest rap cameo of all time goes to KRS-One for putting a stamp on his collaboration with REM and mailing in this weird match-up. Awkward backing vocals throughout the entire song, coupled with an absolute classic gem of a verse to bring it all home at the end…

Check it out
What are you saying
What are you playing
Who are you obeying day out, day in?
Baby, baby, baby, baby
That stuff is driving me crazy
DJs communicate to the masses
Sex and violent classes
Now our children grow up prisoners
All their lives, RADIO LISTENAAAAAAAAAAAAAAAAS

Ladies and gentlemen, the wackest rap cameo of all time.

Stay tuned for next time, when we rank the best buddy cop movies that feature one white cop and one black cop.

…or maybe not.

Honourable mention: Straight To My Feet by Deion Sanders featuring MC Hammer (1994)
This might be the most insane collaboration of all time. This music video features…3 Grammys, a diamond record, 9 Pro Bowl selections, 2 Super Bowl rings, a National League triples title, one Belgium Kickboxing Tournament championship, three MTV Movie Award nominations for Most Desirable Male, and two $100+ million grossing movies. That is pretty fucking insane. That’s not even considering the fact that it’s the only music video for the greatest movie of all time, 1994’s transcendent Street Fighter, a movie that needs no introduction in this space. This is definitely on the shortlist for Best Music Video of all time if even just for Van Damme’s absolutely mind blowing dance moves.

The reason it only makes this post as an honourable mention? There’s absolutely nothing wack about it. There is nothing in this world LESS wack than this video.

They say that two is better than one
But sometimes one is better than two
If you had two heads you’d wish you had one
How is this different?
If you had two dogs attacking you
You’d want just one
There we proved our point!